adapalene

Also known as Differin®, 6-(3-(1-Adamantyl)-4-methoxyphenyl)-2-naphthoic acid, Adaferin, Adapalenum, Adapaleno, Differine

thumb|Adapalene Gel, sold as trade name Differin in China

Key facts

Drug.metabolism: Known to accumulate in the liver and GI-tract. In human, mouse, rat, rabbit, and dog cultured hepatocytes, metabolism appears to affect the methoxybenzene moiety but remains incompletely characterized. The major products of metabolism are glucuronides. Approximately 25% of the drug is metabolized; the rest is excreted as parent drug
Drug.metabolites: Glucuronides
Drug.elimination_half life: between 7 and 51 hours
Drug.excretion: Bile duct
Drug.IUPHAR_ligand: 5429
Drug.CAS_number: 106685-40-9
Drug.PubChem: 60164
Drug.DrugBank: DB00210
Drug.ChemSpiderID: 54244
Drug.UNII: 1L4806J2QF
Drug.KEGG: D01112
Drug.ChEBI: 31174
Drug.ChEMBL: 1265
Drug.IUPAC_name: 6-[3-(1-adamantyl)-4-methoxyphenyl]naphthalene-2-carboxylic acid
Drug.C: 28
Drug.H: 28
Drug.O: 3
Drug.smiles: COC1=C(C=C(C=C1)C2=CC3=C(C=C2)C=C(C=C3)C(=O)O)C45CC6CC(C4)CC(C6)C5

via Wikipedia infobox

Chemical data

Formula: C28H28O3
Molecular weight: 412.5 g/mol
IUPAC name: 6-[3-(1-adamantyl)-4-methoxyphenyl]naphthalene-2-carboxylic acid
SMILES: COC1=C(C=C(C=C1)C2=CC3=C(C=C2)C=C(C=C3)C(=O)O)C45CC6CC(C4)CC(C6)C5
InChIKey: LZCDAPDGXCYOEH-UHFFFAOYSA-N
XLogP: 7.7
Polar surface area: 46.5 Å²
H-bond donors: 1
H-bond acceptors: 3
Formal charge: 0

via PubChem

Research

771 papers

Adapalene.2006
Adapalene/benzoyl peroxide gel 0.3%/2.5% for acne vulgaris.European journal of dermatology : EJD · 2022
Spotlight on adapalene.Expert opinion on drug metabolism & toxicology · 2009
Efficacy and Safety of a Fixed-Dose Clindamycin Phosphate 1.2%, Benzoyl Peroxide 3.1%, and Adapalene 0.15% Gel for Moderate-to-Severe Acne: A Randomized Phase II Study of the First Triple-Combination Drug.American journal of clinical dermatology · 2022
Recent Advances Regarding the Therapeutic Potential of Adapalene.Pharmaceuticals (Basel, Switzerland) · 2020

via PubMed

Wikidata facts

Mass: 412.203845

Show 4 more facts

chemical formula: C₂₈H₂₈O₃
canonical SMILES: COC1=C(C=C(C=C1)C2=CC3=C(C=C2)C=C(C=C3)C(=O)O)C45CC6CC(C4)CC(C6)C5
World Health Organisation international non-proprietary name: adapalene
Commons category: Adapalene

Sources (3)

via Wikidata · CC0

~7 min read

Article

13 sections

Contents

Medical uses
Off-label uses
Cosmetic uses
Side effects
Pregnancy & lactation
Interactions
Pharmacology
Pharmacokinetics
Pharmacodynamics
Metabolism
History
Research
References

thumb|Adapalene Gel, sold as trade name Differin in China

Adapalene, sold under the brand name Differin among others, is a third-generation topical retinoid primarily used in the treatment of mild-moderate acne, and is also used off-label to treat keratosis pilaris as well as other skin conditions. Studies have found adapalene is as effective as other retinoids, while causing less irritation. It also has several advantages over other retinoids. The adapalene molecule is more stable compared to tretinoin and tazarotene, which leads to less concern for photodegradation. It is also chemically more stable compared to the other two retinoids, allowing it to be used in combination with benzoyl peroxide. Due to its effects on keratinocyte proliferation and differentiation, adapalene is superior to tretinoin for the treatment of comedonal acne and is often used as a first-line agent. The Swiss company Galderma developed adapalene.